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Depends on how confident you are in your ability and if you can deal with the prospect of having your passenger get hurt or killed.
Not to be a buzz kill, but that is the reality.
My g/f now rides on the back, but she has no kids/responsibilities, I insist on full gear and make it clear that she is taking her life in her hands. She's a big girl and can make her own decisions and I'm hoping that I can deal with things if we go down. I've been through it before though...
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